Classifications

• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
  • C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
  • C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
  • C07D249/10—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
  • C07D249/12—Oxygen or sulfur atoms
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
  • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
  • C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
• • A—HUMAN NECESSITIES
  • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
  • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
  • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
  • A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
  • A01N43/647—Triazoles; Hydrogenated triazoles
  • A01N43/653—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
  • C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
  • C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
  • C07D249/10—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
  • C07D249/14—Nitrogen atoms
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
  • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
  • C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
  • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
  • C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links

Definitions

• the invention relates to new 1-aryltriazolin (thi) one, several processes for their preparation, several new intermediates and their use as herbicides.
• the 1-aryltriazolin (thi) ones of the general formula (I) according to the invention show a considerably better herbicidal activity against problem weeds with comparable tolerance to useful plants compared to the substituted triazolinones known from the prior art, such as the compound 3-methyl- 4-propargyl-1- (2,5-difluoro-4-cyano-phenyl) -1,2,4-triazolin-5-one, which are chemically and functionally obvious compounds.
• the course of the reaction of process (a) according to the invention can be represented by the following formula: If, for example, 1- (4-cyano-2,5-difluorophenyl) -4-methyl-3-dimethylamino-1,2,4-triazolin-5-one and 1-butyn-3-ol are used as starting materials, then represent the course of the reaction of process (b) according to the invention using the following formula: If, for example, 1- (4-cyano-2-fluoro-5-methoxy-phenyl) -4-amino-3-dimethyamino-1,2,4-triazolin-5-one and sodium nitrite are used as starting materials, the reaction can be carried out of process (c) according to the invention using the following formula: If, for example, 1- (4-cyano-2-fluoro-5-methoxy-
• 1H-triazolinones of the formula (II) are obtained by a process which has hitherto not been known if chloroformamide hydrochlorides of the formula (VI) in which R2, R8 and R9 have the meanings given above, with carbazates of the formula (IX), H2N-NH-CO-O-R1 (IX) in which R1 has the meaning given above, if appropriate in the presence of a diluent such as acetonitrile and if appropriate in the presence of a reaction auxiliary such as sodium bicarbonate at temperatures between -20 ° C and + 100 ° C (see also the preparation examples).
• Formula (III) provides a general definition of the halogenobenzene derivatives also required as starting materials for carrying out process (a) according to the invention.
• R3, R4, R5, R6 and R7 are preferably and particularly preferably those radicals which have already been preferred in connection with the description of the compounds of the formula (I) and were particularly preferred for these substituents.
• Hal1 is preferably fluorine, chlorine or bromine, especially fluorine or chlorine.
• the halogenobenzene derivatives of the formula (III) are generally known or can be obtained in analogy to known processes (cf., for example, EP 191 181; EP 441 004; EP 431 373).
• the compound 5-chloro-2,4-difluorobenzonitrile is not yet known. They are obtained when the known compound 2,4,5-trichlorobenzonitrile (see, for example, EP 441 004) is reacted with potassium fluoride, if appropriate in the presence of a diluent such as, for example, tetramethylene sulfone, at temperatures between 100 ° C. and 200 ° C. Manufacturing examples).
• a diluent such as, for example, tetramethylene sulfone
• Formula (Ia) provides a general definition of the substituted triazolinones required as starting material for carrying out process (b) according to the invention.
• R1, R2, R3, R5, R6, R7 and X preferably and particularly preferably represent those radicals which have been preferred and particularly preferred for these in connection with the description of the substances of the formula (I) according to the invention Substituents were called.
• Hal2 is preferably fluorine, chlorine or bromine, especially fluorine or chlorine.
• the substituted triazolinones of the formula (Ia) are compounds according to the invention and can be obtained with the aid of processes (a), (c), (d) and / or (e) according to the invention.
• Formula (IV) provides a general definition of the nucleophiles which are furthermore required as starting materials for carrying out process (b) according to the invention.
• R13 preferably represents a radical of the formula -O-R12, -S-R12 or -NR11R12, wherein R11 and R12 preferably represent those radicals which have already been associated with the description of the substances of the formula ( I) have been mentioned as preferred and particularly preferred for these substituents.
• the nucleophiles of the formula (IV) are generally known compounds of organic chemistry.
• Formula (Ib) provides a general definition of the substituted triazolinones required as starting materials for carrying out process (c) according to the invention.
• R1, R3, R4, R5, R6, R7 and X are preferably and particularly preferably those radicals which, in connection with the description of the substances of the formula (I) according to the invention, are preferred and particularly preferred for these substituents were called.
• the substituted triazolinones of the formula (Ib) are compounds according to the invention and can be obtained with the aid of processes (a), (b) and / or (e) according to the invention.
• Formula (Ic) provides a general definition of the substituted triazolinones required as starting materials for carrying out process (d) according to the invention.
• R1, R3, R4, R5, R6, R7 and X are preferably and particularly preferably those radicals which, in connection with the description of the substances of the formula (I) according to the invention, are preferred and particularly preferred for these Substituents were called.
• the substituted triazolinones of the formula (Ic) are compounds according to the invention and can be obtained with the aid of processes (a), (b), (c) and / or (e) according to the invention.
• Formula (V) provides a general definition of the alkylating agents which are furthermore required as starting materials for carrying out process (d) according to the invention.
• R2 ⁇ 1 preferably and particularly preferably represents those radicals which have already been mentioned as preferred and particularly preferred for the substituents R10 in connection with the description of the substances of the formula (I) according to the invention, with the exception of the optionally substituted ones Aryl or heterocyclyl residues.
• E1 is preferably a leaving radical customary in alkylating agents, such as halogen, in particular chlorine, bromine or iodine, or optionally substituted alkylsulfonyloxy, alkoxysulfonyloxy or arylsulfonyloxy, such as in particular methanesulfonyloxy, trifluoromethanesulfonyloxy, methoxysulfonyloxy, ethoxysulfonyloxy or p-toluenesulfonyloxy.
• the alkylating agents of the formula (V) are generally known compounds of organic chemistry.
• Formula (VI) provides a general definition of the chloroformamide hydrochlorides required to carry out process (e) according to the invention.
• R2, R8 and R9 preferably and particularly preferably represent those radicals which have already been mentioned as preferred and particularly preferred for these substituents in connection with the description of the substances of the formula (I) according to the invention.
• the chloroformamide hydrochlorides of the formula (VI) are known or can be obtained in analogy to known processes (cf. eg EP 283 876; EP 398 097; Chem. Ber. 97 , 1232 [1964]).
• Formula (VII) provides a general definition of the arylhydrazines which are furthermore required as starting materials for carrying out process (e) according to the invention.
• R3, R4, R5, R6 and R7 are preferably and particularly preferably those radicals which have already been mentioned as preferred and particularly preferred for these substituents in connection with the description of the substances of the formula (I) according to the invention
• the arylhydrazines of the formula (VII) are generally known compounds of organic chemistry, or can be obtained analogously to known processes (cf., for example, Houben-Weyl "Methods of Organic Chemistry", Thieme Verlag Stuttgart, Volume X / 2, p. 180, 201 , 245; Angew. Chem. 80 , 284 [1968]; Chem. Ber. 102 , 3088 [1969]; DE 33 37 543; DE 34 02 308; DE 34 47 211; DE 39 03 799).
• Inert organic solvents are suitable as diluents for carrying out process (a) according to the invention.
• These include in particular aliphatic, alicyclic or aromatic, optionally halogenated hydrocarbons, such as, for example, gasoline, benzene, toluene, xylene, chlorobenzene, dichlorobenzene, petroleum ether, hexane, cyclohexane, dichloromethane, chloroform or carbon tetrachloride; Ethers such as diethyl ether, diisopropyl ether, dioxane, tetrahydrofuran or ethylene glycol dimethyl or diethyl ether; Ketones, such as acetone, butanone or methyl isobutyl ketone; Nitriles such as acetonitrile, propionitrile or benzonitrile; Amides, such as N, N-dimethylformamide, N, N-dimethylacetamide, N
• Process (a) according to the invention is preferably carried out in the presence of a suitable reaction auxiliary.
• All conventional inorganic or organic bases are suitable as such. These include, for example, alkaline earth metal or alkali metal hydroxides, such as sodium hydroxide, calcium hydroxide, potassium hydroxide or also ammonium hydroxide, alkali metal carbonates, such as sodium carbonate, potassium carbonate, potassium hydrogen carbonate, sodium hydrogen carbonate or ammonium carbonate, alkali metal or alkaline earth metal acetates, such as sodium acetate, potassium acetate, calcium acetate, and also ammonium acetate or ammonium acetate Trimethylamine, triethylamine, Tributylamine, N, N-dimethylaniline, pyridine, piperidine, N-methylpiperidine, N, N-dimethylaminopyridine, diazabicyclooctane (DABCO), diazabicyclonones (DBN) or diazabicyclounde
• reaction temperatures can be varied within a substantial range when carrying out process (a) according to the invention. In general, temperatures between 0 ° C and + 180 ° C, preferably at temperatures between + 20 ° C and + 120 ° C.
• Process (a) according to the invention is usually carried out under normal pressure. However, it is also possible to work under increased or reduced pressure.
• 1.0 to 3.0 mol, preferably 1.0 to 1.5 mol, of halogenobenzene derivative of the formula (III) and, if appropriate, are generally employed per mol of 1H-triazolinone of the formula (II) 1.0 to 3.0 mol, preferably 1.0 to 1.5 mol, of base as reaction auxiliary.
• the reaction is carried out, worked up and isolated using generally customary, known processes (see also the preparation examples).
• Inert organic solvents are suitable as diluents for carrying out process (b) according to the invention.
• the solvents listed in the description of the implementation of process (a) according to the invention are preferably used.
• Process (b) according to the invention is preferably carried out in the presence of a suitable reaction auxiliary.
• All conventional inorganic or organic bases are suitable as such. These include, for example, alkaline earth metal or alkali metal hydrides, hydroxides, amides, alcoholates, acetates, carbonates or hydrogen carbonates, such as sodium hydride, sodium amide, sodium methylate, sodium ethylate, potassium tert-butoxide, sodium hydroxide, potassium hydroxide, ammonium hydroxide, sodium acetate , Potassium acetate, calcium acetate, ammonium acetate, sodium carbonate, potassium carbonate, potassium hydrogen carbonate, sodium hydrogen carbonate or ammonium carbonate and also tertiary amines, such as trimethylamine, triethylamine, tributylamine, N, N-dimethylaniline, pyridine, N-methylpiperidine, N, N-dimethylaminopyridine, Diazabicyclooctane
• reaction temperatures can be varied within a substantial range when carrying out process (b) according to the invention. In general, temperatures between -20 ° C and + 150 ° C, preferably at temperatures between 0 ° C and + 120 ° C.
• Process (b) according to the invention is usually carried out under normal pressure. However, it is also possible to work under increased or reduced pressure.
• nucleophile of the formula (IV) and, if appropriate, 0.1 are generally employed per mol of substituted triazolinone of the formula (Ia) to 3.0 mol, preferably 1.0 to 1.5 mol, of base as reaction auxiliary.
• the reaction is carried out, worked up and isolated by generally customary, known processes (see also the preparation examples).
• Process (c) according to the invention is usually carried out in the presence of a suitable acid.
• Aqueous mineral acids are particularly suitable as such.
• Dilute hydrochloric acid is particularly preferred.
• Suitable diluents for carrying out process (c) according to the invention are all diluents customary for such diazotization reactions. Particular preference is given to using the aqueous mineral acids used as reagents, such as, for example, hydrochloric acid in a corresponding excess, as diluents.
• reaction temperatures can be varied within a substantial range when carrying out process (c) according to the invention. In general, temperatures between -20 ° C and + 100 ° C, preferably at temperatures between -10 ° C and + 80 ° C.
• Process (c) according to the invention is usually carried out under normal pressure. However, it is also possible to work under increased or reduced pressure.
• Inert organic solvents are suitable as diluents for carrying out process (d) according to the invention.
• diluents for carrying out process (d) according to the invention.
• These include in particular aliphatic, alicyclic or aromatic optionally halogenated hydrocarbons, such as, for example, gasoline, benzene, toluene, xylene, chlorobenzene, dichlorobenzene, petroleum ether, hexane, cyclohexane, dichloromethane, chloroform, carbon tetrachloride; Ethers such as diethyl ether, diisopropyl ether, dioxane, tetrahydrofuran or ethylene glycol dimethyl or diethyl ether; Ketones such as acetone, butanone or methyl isobutyl ketone; Nitriles such as acetonitrile, propionitrile or benzonitrile; Amides such as N, N-d
• process (d) according to the invention can also be carried out in a two-phase system, such as, for example, water / toluene or water / dichloromethane, if appropriate in the presence of a suitable phase transfer catalyst.
• suitable phase transfer catalysts may be mentioned are: tetrabutylammonium iodide, tetrabutylammonium bromide, tetrabutylammonium chloride, tributyl methylphosphonium, trimethyl-C13 / C15--alkylammonium, trimethyl-C13 / C15-alkylammonium, dibenzyl dimethyl ammonium methyl sulfate, dimethyl-C12 / C14-alkyl benzyl ammonium chloride, Dimethyl-C12 / C14-alkyl-benzylammonium bromide, tetrabutylammonium hydroxide, triethylbenzylammonium chloride, methyl
• Process (d) according to the invention is preferably carried out in the presence of a suitable reaction auxiliary.
• All conventional inorganic or organic bases are suitable as such. These include, for example, alkaline earth metal or alkali metal hydrides, hydroxides, amides, alcoholates, acetates, carbonates or hydrogen carbonates, such as sodium hydride, sodium amide, sodium methylate, sodium ethylate, potassium tert-butoxide, sodium hydroxide, potassium hydroxide, ammonium hydroxide, sodium acetate , Potassium acetate, calcium acetate, ammonium acetate, sodium carbonate, potassium carbonate, potassium hydrogen carbonate, sodium hydrogen carbonate or ammonium carbonate and tertiary amines such as trimethylamine, triethylamine, tributylamine, N, N-dimethylaniline, pyridine, N-methylpiperidine, N, N-dimethylaminopyridine, diazabicyclooctane (d
• reaction temperatures can be varied within a substantial range when carrying out process (d) according to the invention. In general, temperatures between -20 ° C and + 150 ° C, preferably at temperatures between 0 ° C and + 120 ° C.
• Process (d) according to the invention is usually carried out under normal pressure. However, it is also possible to work under increased or reduced pressure.
• Inert organic solvents are suitable as diluents for carrying out the 1st stage of process (e) according to the invention.
• These include in particular aliphatic, alicyclic or aromatic, optionally halogenated hydrocarbons, such as, for example, gasoline, benzene, toluene, xylene, chlorobenzene, dichlorobenzene, petroleum ether, hexane, cyclohexane, dichloromethane, chloroform or carbon tetrachloride; Ethers such as diethyl ether, diisopropyl ether, dioxane, tetrahydrofuran or ethylene glycol dimethyl or diethyl ether; Ketones, such as acetone, butanone or methyl isobutyl ketone; Nitriles such as acetonitrile, propionitrile or benzonitrile; Amides, such as N, N-dimethylformamide, N, N-di
• reaction temperatures can be varied within a substantial range when carrying out stage 1 of process (e) according to the invention. In general, temperatures between -20 ° C and + 100 ° C, preferably at temperatures between 0 ° C and + 80 ° C.
• the first stage of process (e) according to the invention is usually carried out under normal pressure. However, it is also possible to work under increased or reduced pressure.
• Inert organic solvents are also suitable as diluents for carrying out the second stage of process (e) according to the invention.
• These include in particular aliphatic, alicyclic or aromatic, optionally halogenated hydrocarbons, such as, for example, gasoline, benzene, toluene, xylene, chlorobenzene, dichlorobenzene, petroleum ether, hexane, cyclohexane, dichloromethane, chloroform or carbon tetrachloride; Ethers such as diethyl ether, diisopropyl ether, dioxane, tetrahydrofuran or ethylene glycol dimethyl or diethyl ether; Ketones, such as acetone, Butanone or methyl isobutyl ketone; Nitriles such as acetonitrile, propionitrile or benzonitrile; Amides, such as N, N-dimethylformamide, N, N-dimethyl
• reaction temperatures can be varied within a substantial range when carrying out stage 2 of process (e) according to the invention. In general, temperatures between -20 ° C and + 100 ° C, preferably at temperatures between 0 ° C and + 80 ° C.
• the second stage of process (e) according to the invention is usually carried out under normal pressure. However, it is also possible to work under increased or reduced pressure.
• the end products of the formula (I) are purified by means of customary processes, for example by column chromatography, or by recrystallization.
• the characterization is carried out using the melting point or, in the case of non-crystallizing compounds, using proton nuclear magnetic resonance spectroscopy (1 H-NMR).
• the active compounds according to the invention can be used as defoliants, desiccants, haulm killers and in particular as weed killers. Weeds in the broadest sense are all plants that grow in places where they are undesirable. Whether the substances according to the invention act as total or selective herbicides depends essentially on the amount used.
• the active compounds according to the invention can be used, for example, in the following plants: Dicotyledon weeds of the genera: Sinapis, Lepidium, Galium, Stellaria, Matricaria, Anthemis, Galinsoga, Chenopodium, Urtica, Senecio, Amaranthus, Portulaca, Xanthium, Convolvulus, Ipomoea, Polygonum, Sesbania, Ambrosia, Cirsium, Carduus, Sonchus, Solanum, Rorippa, Rotala, Lindernia, Lamium, Veronica, Abutilon, Emex, Datura, Viola, Galeopsis, Papaver, Centaurea, Trifolaxac, Ranunculus.
• the compounds are suitable for total weed control, e.g. on industrial and track systems and on paths and squares with and without tree cover.
• the compounds for weed control in permanent crops e.g. Forests, ornamental trees, fruit, wine, citrus, nut, banana, coffee, tea, rubber, oil palm, cocoa, berry fruit and hop plants and for selective weed control in annual crops.
• the active compounds according to the invention can be used particularly successfully to control dicotyledon weeds in monocotyledon crops such as, for example, wheat or corn.
• the active compounds according to the invention also have foliar insecticidal and acaricidal activity in appropriate amounts.
• the active ingredients can be converted into the customary formulations, such as solutions, emulsions, suspensions, powders, foams, pastes, granules, aerosols, active ingredient-impregnated natural and synthetic substances, very fine encapsulations in polymers Fabrics and in coating compositions for seeds, also in formulations with fuel sets, such as smoking cartridges, cans, spirals and the like, as well as ULV cold and warm mist formulations.
• the customary formulations such as solutions, emulsions, suspensions, powders, foams, pastes, granules, aerosols, active ingredient-impregnated natural and synthetic substances, very fine encapsulations in polymers Fabrics and in coating compositions for seeds, also in formulations with fuel sets, such as smoking cartridges, cans, spirals and the like, as well as ULV cold and warm mist formulations.
• formulations are prepared in a known manner, for example by mixing the active ingredients with extenders, that is to say liquid solvents, pressurized liquefied gases and / or solid carriers, optionally using surface-active agents, that is to say emulsifiers and / or dispersants and / or foam-generating agents. If water is used as an extender, organic solvents can, for example, also be used as auxiliary solvents.
• extenders that is to say liquid solvents, pressurized liquefied gases and / or solid carriers, optionally using surface-active agents, that is to say emulsifiers and / or dispersants and / or foam-generating agents.
• surface-active agents that is to say emulsifiers and / or dispersants and / or foam-generating agents.
• organic solvents can, for example, also be used as auxiliary solvents.
• liquid solvents aromatics, such as xylene, toluene or alkylnaphthalenes, chlorinated aromatics or chlorinated aliphatic hydrocarbons, such as chlorobenzenes, chlorethylenes or methylene chloride, aliphatic hydrocarbons, such as cyclohexane or paraffins, for example petroleum fractions, alcohols, such as butanol or glycol, and the like Ethers and esters, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents such as dimethylformamide and dimethyl sulfoxide, and water;
• Liquefied gaseous extenders or carriers mean liquids which are gaseous at normal temperature and under normal pressure, for example aerosol propellants such as halogenated hydrocarbons and butane, propane, nitrogen and carbon dioxide;
• Solid carrier materials are suitable: for example natural rock powders such as
• Adhesives such as carboxymethyl cellulose, natural and synthetic powdery, granular or latex-shaped polymers, such as gum arabic, polyvinyl alcohol, polyvinyl acetate, and also natural phospholipids, such as cephalins and lecithins, and synthetic phospholipids can be used in the formulations.
• Other additives can be mineral and vegetable oils.
• Dyes such as inorganic pigments, e.g. Iron oxide, titanium oxide, ferrocyan blue and organic dyes such as alizarin, azo and metal phthalocyanine dyes and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and tin can be used.
• inorganic pigments e.g. Iron oxide, titanium oxide, ferrocyan blue and organic dyes such as alizarin, azo and metal phthalocyanine dyes and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and tin can be used.
• the formulations generally contain between 0.1 and 95 percent by weight of active compound, preferably between 0.5 and 90%.
• the active compounds according to the invention can also be used in a mixture with known herbicides for weed control, finished formulations or tank mixes being possible.
• known herbicides are suitable for the mixtures, for example anilides, such as, for example, diflufenican and propanil; Aryl carboxylic acids, such as dichloropicolinic acid, dicamba or picloram; Aryloxyalkanoic acids such as 2,4-D, 2,4-DB, 2,4-DP, fluroxypyr, MCPA, MCPP and triclopyr; Aryloxy-phenoxy-alkanoic acid esters, such as, for example, diclofop-methyl, fenoxaprop-ethyl, fluazifop-butyl, haloxyfop-methyl and quizalofopethyl; Azinones such as chloridazon and norflurazon; Carbamates such as chlorpropham, desmedipham, phenmedipham and propham; Ch
• a mixture with other known active compounds such as fungicides, insecticides, acaricides, nematicides, bird repellants, plant nutrients and agents which improve soil structure, is also possible.
• the active compounds can be used as such, in the form of their formulations or in the use forms prepared therefrom by further dilution, such as ready-to-use solutions, suspensions, emulsions, powders, pastes and granules. They are used in the usual way, e.g. by pouring, spraying; Spray, sprinkle.
• the active compounds according to the invention can be applied both before and after emergence of the plants. They can also be worked into the soil before sowing.
• the amount of active ingredient used can vary over a wide range. It essentially depends on the type of effect desired. In general, the application rates are between 0.01 and 10 kg of active ingredient per hectare of soil, preferably between 0.05 and 5 kg per hectare.
• 0.24 g (0.006 mol) of sodium hydride (60% in paraffin oil) is added to 0.42 g (0.006 mol) of 3-butyn-1-ol in 50 ml of acetonitrile at room temperature, stirred for 10 minutes at room temperature, then Add 2 g (0.0043 mol) of 1- (4-cyano-2,5-difluorophenyl) -4-methyl-3-dimethylamino-1,2,4-triazolin-5-one and stir for a further 2 hours at room temperature.
• reaction mixture is filtered, the filtrate is concentrated in vacuo, the residue is partitioned between dichloromethane and water, the organic phase is separated off, dried over sodium sulfate, concentrated in vacuo and crystallized by stirring with a little methanol.
• 220 g (1.06 mol) of 2,4,5-trichlorobenzonitrile (see, for example, EP 441 004) are added to 250 g (4.31 mol) of potassium fluoride in 400 ml of distilled tetramethylene sulfone while stirring at room temperature, and the mixture is then stirred for 10 hours 195 ° C to 200 ° C.
• the mixture is cooled, 500 ml of water are added and the mixture is subjected to steam distillation. The organic portion is taken up in dichloromethane, dried over sodium sulfate, concentrated in vacuo and distilled.

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• Chemical & Material Sciences (AREA)
• Organic Chemistry (AREA)
• Life Sciences & Earth Sciences (AREA)
• Agronomy & Crop Science (AREA)
• Pest Control & Pesticides (AREA)
• Plant Pathology (AREA)
• Health & Medical Sciences (AREA)
• Engineering & Computer Science (AREA)
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• Wood Science & Technology (AREA)
• Zoology (AREA)
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• Plural Heterocyclic Compounds (AREA)
• Agricultural Chemicals And Associated Chemicals (AREA)

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• 1993
  • 1993-02-09 DE DE4303676A patent/DE4303676A1/de not_active Withdrawn
• 1994
  • 1994-01-27 EP EP94101222A patent/EP0610733A1/fr not_active Ceased
  • 1994-02-02 US US08/190,813 patent/US5476946A/en not_active Expired - Fee Related
  • 1994-02-02 TW TW083100855A patent/TW242107B/zh active
  • 1994-02-04 CA CA002115017A patent/CA2115017A1/fr not_active Abandoned
  • 1994-02-04 JP JP6031978A patent/JPH06306060A/ja active Pending
  • 1994-02-04 KR KR1019940002131A patent/KR940019694A/ko not_active Application Discontinuation
  • 1994-02-08 BR BR9400462A patent/BR9400462A/pt not_active Application Discontinuation
  • 1994-02-08 HU HU9400351A patent/HUT72171A/hu unknown
  • 1994-02-09 CN CN94101567A patent/CN1092065A/zh active Pending

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